On leaving school Milton Allen was apprentice to a tailor in Basseterre and then emigrated to the United States in search of a better future. In 1937 he married Annie Locker, Head Teacher at the Sandy Point Girls’ School and supported the school’s extra-curricular activities by sending her much needed sheet music. He wrote poetry and from time to time contributed items to The Union Messenger often expressing concerns regarding the well-being of workers.
Bradshaw recalled how in 1935 Milton Allen then living in New York, had gone around, along with other Kittitians living there, collecting money for the purpose of securing the services of a lawyer to defend
workers who had been arrested and charged for rioting for higher wages and better conditions of life in January of 1935. The money they collected was sent here and used to ensure that the people charged for rioting had full legal representation.
Allen served as a member of the Legislative Council from 1958 to 1962. That year saw the termination of the West Indies Federation and the return of Robert Bradshaw to St. Kitts. Allen resigned his seat so that Bradshaw could return to the Legislative Council. He was later appointed speaker of the House of Assembly. In 1969, Milton Allen became the first native of St. Kitts to be appointed Governor of the Associated State of St. Kitts, Nevis and Anguilla.